S-Ruxolitinib (INCB018424)

Base Information

• Chemical Name: S-Ruxolitinib (INCB018424)
• CAS No.: 941685-37-6
• Molecular Formula: C₁₇H₁₈N₆
• Molecular Weight: 306.37
• Mol file: 941685-37-6.mol

Synonyms:S-Ruxolitinib (INCB018424);Ruxolitinib (S enantioMer);(3S)-3-Cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyriMidin-4-yl)-1H-pyrazol-1-yl]propanenitrile;S-Ruxolitinib;INCB 18424;1H-Pyrazole-1-propanenitrile, β-cyclopentyl-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-, (βS)-

Chemical Property of S-Ruxolitinib (INCB018424)

Chemical Property:

• PSA: 83.18000
• LogP: 3.46638
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99%+, ^*data from raw suppliers

(3S)-3-Cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile(ent-Ruxolitinib) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (3S)-3-Cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile is a newly developed JAK2 inhibitor therapy aimed to improve MPN-associated splenomegaly and systemic symptoms. (3S)-3-Cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile is a newly developed JAK2 inhibitor therapy aimed to improve MPN-associated splenomegaly and systemic symptoms. The opposite enantiomer of Ruxolitinib (R702000).

Technology Process of S-Ruxolitinib (INCB018424)

There total 92 articles about S-Ruxolitinib (INCB018424) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(R)-(4-(1-(2-cyano-1-cyclopentylethyl)-1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate (1146629-80-2) → ruxolitinib (941678-49-5,941685-37-6)

Guidance literature:

With water; sodium hydroxide; In methanol; at 20 ℃; Product distribution / selectivity;

Reference yield: 92.1%

(3R)-3-cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (941685-40-1) → ruxolitinib (941678-49-5,941685-37-6)

Guidance literature:

(3R)-3-cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile; With boron trifluoride diethyl etherate; In acetonitrile; at 60 - 70 ℃; for 5h;

With ammonium hydroxide; water; In acetonitrile; at 20 ℃; for 12h;

Reference yield: 77.3%

(R)-3-(4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopentylpropionamide → ruxolitinib (941678-49-5,941685-37-6)

Guidance literature:

With trichlorophosphate; In 1-methyl-pyrrolidin-2-one; dichloromethane; at 20 - 30 ℃; for 3h;

upstream raw materials:

racemic-3-cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile

(3R)-3-cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile

(R)-(4-(1-(2-cyano-1-cyclopentylethyl)-1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate

(3R)-3-cyclopentyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propanenitrile

Refernces

• 1、 Davis, Ryan R.,Li, Baoli,Yun, Sang Y.,Chan, Alice,Nareddy, Pradeep,Gunawan, Steven,Ayaz, Muhammad,Lawrence, Harshani R.,Reuther, Gary W.,Lawrence, Nicholas J.,Sch?nbrunn, Ernst. "Structural Insights into JAK2 Inhibition by Ruxolitinib, Fedratinib, and Derivatives Thereof". . p. 2228 - 2241. Retrieved 2021/03/01.
• 2、 -. "SYNTHESIS PROCESS OF RUXOLITINIB". Paragraph 0278-0280. . Retrieved 2019/02/05.